hihi!
coming off spending the weekend in Hudson—a creative haven about two hours from New York that’s long attracted collectors, artists, and makers—I’ve been thinking a whole lot about what it means to claim to be “creative” as a part of your identity. as someone who runs marathons but can barely call themselves an athlete without cringing, there’s no certainly concrete creative act that’s afforded me license to fully claim creativity as a part of my being. there is no quantifiable creativity threshold (finishing and hanging a painting on a wall? publishing a book? sipping out of a mug I fired myself?) that I feel I’ve surpassed that gives me the right to do so. but I think that’s exactly the point. there is no “pass go, you get to call yourself a creative.” you just do.
so, let me take a big leap to cement the basis of this essay: I’m a writer.
despite growing up as the kid in elementary school who was told they had an aptitude for writing, spending the last two decades gravitating towards “liberal arts” over math and science, and nearly a decade spent working in marketing—with a fair bit of my daily work focused on copywriting—it took me until recently to be able to confidently say, “I’m a writer.”
just because I say it, does that make my self-proclaimed identity as a writer true? does publishing weekly content on Substack make me a writer? or does the fact that I look after editorial strategy and output for a leading travel company make me a writer? is it the someone PAYING for my writing that actually makes me a writer? I would argue no. I’m of the belief that whether you create for yourself and that art never leaves the confines of your bedroom or whether you share your work with a community you’ve cultivated, creativity is rooted in just making the thing. and that act is one deeply rooted in vulnerability.
I’m also of the belief that there is room for everyone to be creative. and if you’re a capitalist like me, you might also be of the mind that you have the right to monetize that creativity—but that’s not necessarily an opinion held by all. the discourse on Substack (if you get my newsletter straight into your inbox and have no idea what it means when it says “Read In App” up top—Substack is the distribution platform that the sunday series is built on) this past week or so has been evidence of that.
if you’re like, wait, what are you talking about?? allow me to be more specific. ’s recent Substack essay, “The machine in the garden.” goes into depth about “why ‘writer’ has become such an easy job title to give oneself.” in this essay, she gets at the heart of why I (and so many others on this platform who are putting out their work—often for FREE) struggle to fully own the self-proclaimed title of ‘writer.’ and while I’d encourage you to read (and engage with!) her take in its entirety, let me share a snippet. she writes,
I’m noticing this platform has become a really good way for women to monetize their diary entries — lists, random thoughts, and (easy to write) roundups of “what I’ve been doing” do really well on this site. Substack is making everyone into writers the same way Instagram made everyone into photographers…
Emily goes on to analyze the seeming diminishing quality of the writing on this platform as more and more get on board, particularly as it relates to paid Substacks (of which, the sunday series will be joining the ranks when I turn on a paywall for select sends starting in September!!!!). for me, reading her thoughts on the matter were, well, triggering. it felt like a different version of the ongoing cultural conversation those of us who’ve long loved “women’s fiction” or following fashion bloggers have been having…does something being easily consumable—be it a romcom, a listicle, or a trend roundup—mean that it’s not worthy of being called creative? does it mean that just because it’s not ‘high brow’ art, it’s not art worth celebrating?
let me caveat this all by saying I love Emily’s work. she publishes
daily, diving into culture through the lens of business, which just so happens to be my ideal web of interest. so I get why—as someone whose profession is dedicated to producing daily, thought-provoking, and research-based content on this platform—she’d have a thing or two to say about how diary-style Substacks feel, for lack of a better word, lazy.but I can also recognize that it’s not a bad thing that her essay got to the root of many of my creative insecurities. interestingly, for me, this reckoning came at the exact time when I’m looking to transition from producing this weekly send completely for free to, yes, charging a nominal fee to protect my time as I aim to deliver greater value on this platform. do I think Emily’s intention was to make me and so many others feel bad about our own AUDACITY to proclaim ourselves writers? no. but I do think that if you’re going to have the chutzpah to ask people to pay for your “silly” little lists and recommendations, you’ve got to be ready for this kind of questioning. and so here I am, giving it deeper thought on this open forum where comments are encouraged…no really, please comment, it makes it feel like this is less of a void!
but it wasn’t just me questioning the essence of “the machine in the garden.” there were hundreds of comments, sooooo much discourse across the Notes feature of Substack, and many, many mentions of the essay in other Substacks I diligently follow on the topic of monetization. I particularly appreciated
and ’s takes on it. in different ways, they both got at the complex dichotomy of the ‘cool girl’ versus, as Grace put it, ‘Lady Lowbrow’ (LOVE) content. I’d squarely put my Substack in the latter half, and perhaps that’s the entire point.I’ve spilled my heart out on here on essays about money (!!), delved into comparison spirals, and shared things I’m personally struggling with, but you know which posts get the most engagement? the ones where I round up my favorite places to eat in paris. the ones where I tell you what I did in mexico city. the ones where I tell you my favorite podcasts of the moment. the ones where I’ve broken down my top reads over the past the year. also known as…listicles. though, granted, listicles that required a great deal of my curation, investment in travel, and personal cultural lens to acquire.
so that’s what we’re going to keep doing. I’m going to keep creating the content that resonates for me as a writer but, ultimately, for you as my valued reader. I’m excited to explore how I can create even more valuable sends for my paid subscribers this fall, particularly as I dive into six weeks of travel, the back half of marathon training, and the culmination of a creative project I’ve been working on for quite some time that I can’t wait to share…when the time is right.
but in the meantime, I’ll be over here admiring the broom (yes, like one you sweep with) I handmade in Hudson during a workshop at Stissing House knowing that no, one broom made does not make me a broom-maker. but it does make me someone who’s willing to try, and be seen trying at that. xKD
Meet Michelle Wintersteen
I’ve followed Michelle over at @mkwcreative.co for years and seen her behind the creative of some of my favorite brands (hello, Hotel Lobby Candle!), so when brainstorming who I was going to bring on during my August “summer school” series, I knew I wanted to feature her career trajectory. I absolutely loved her candor in our Q&A and hope you do, too! plus, for all my entrepreneur friends who are constantly asking for support in the branding arena, Michelle is the best of the best. and don’t worry, I already asked her what her waitlist looks like! she shared that she’s taking on new projects with October and November start dates!
Kayla Douglas: Michelle, before we wind back through your career path, tell us a bit about what you do today through your work at MKW Creative Co.
Michelle Wintersteen: Today, as the founder and creative director of MKW Creative Co., I lead a dynamic team that specializes in crafting compelling brand identities, executing impactful social media strategies, and designing eye-catching print and merch. Our core mission is to help build what we call brag-worthy brands. We work closely with our clients to not only create visually stunning designs but also to ensure that every element of their brand is aligned with their overarching business goals. Whether it's launching a new product or rebranding an established company, my team and I are passionate about driving creative strategies that make a real difference.
KD: What were some early career choices that led you to the design world?
MW: I took an unconventional path into the design world, starting my business at just 20 years old while still a college student. Back then, I was charging $15 an hour and learning everything I could from podcasts and YouTube tutorials. That early hustle taught me the value of self-education and being adaptable—skills that have been essential as I’ve grown MKW Creative Co. into what it is today. I've always been an avid networker and connected with entrepreneurs and agencies early on who taught me a lot about branding and how to scale. From year 3-6 I was a digital nomad, working and living remotely from all over the world and exposing myself to different people and cultures, which greatly helped expand my skill set and impact.
KD: How do you approach building brand-worthy brands for hospitality, creative lifestyle business owners, and product-based brands?
MW: When building brand-worthy identities for hospitality, creative lifestyle businesses, and product-based brands, my approach is centered around deeply understanding the essence of each brand. I start by diving into the unique story, values, and vision of the business. For hospitality brands, it’s about capturing the atmosphere and experience they offer. For creative lifestyle businesses, I focus on showcasing their personality and what makes them stand out. With product-based brands, I emphasize the product's story and its connection with the target audience. From there, it’s all about translating those elements into a cohesive visual identity and brand strategy that resonates with the target audience. I believe in creating brands that not only look great but also communicate the right message and evoke the desired emotions. The goal is always to craft a brand experience that feels authentic and engaging at every touchpoint.
KD: In addition to being highly active on social, you also have a podcast. How do you approach treating content creation for MKW Creative Co. as an integral part of the business without burning out?
MW: Burnout as a creative is somewhat unavoidable because as you build, the problems that were once hard become easy, but the new problems require way more brain power. Now with ten years under my belt, I've learned to create a system where I work in advance (very unnatural to me) by producing the Kiss My Aesthetic Podcast. By batching episodes and planning ahead, I ensure there’s always fresh content ready to go, even if I'm not "feeling it" on the day that it's going live. I also build accountability with my audience by committing to a weekly podcast episode, no matter what (and paying a team to make sure it happens). This consistency helps keep the momentum going without overwhelming myself.
KD: What does an average "day in the life" look like?
MW: As I'm sure many creatives can relate, no two days are the same and I like it that way. Typically, when I'm in San Diego, my mornings start with breakfast and a power hour of getting my life together (cleaning, talking to my sis on the phone, listening to a podcast, etc.). Then most days I'm checking in with my team first thing to see what they need. From there, I will also schedule out virtual coworks with specific team members based on the projects on the docket. After lunch is usually dedicated to client meetings or design time, and I'm usually brain dead by about 4:30pm which is when I leave for my workout. Post-workout it's an hour long dog walk + a podcast or phone call to family or friends... back home for dinner, then maybe a bit more work from the couch. I'm holding myself to a strict 10pm laptop power-off rule recently so that I can give my brain enough of a break before bed because I notice I reeeeally feel it if I stay up too late. Weekends are dedicated to being outside, eating fresh food, being at the beach and seeing my fam!
KD: Personal Q now! As a HUGE proponent of the birthday trip, I was dying over the branding for your 30th birthday trip to Italy. What inspired the trip and, ultimately, the design aesthetic you brought into making the swag so special for your friends?
MW: My friends were given 5+ years warning that this was happening, so no one was surprised when they got the invite. My 30th birthday felt like a milestone worth celebrating in a big way, so I chose Italy because 1) I'm obsessed 2) I've gone 15+ times in the last 5 years and 3) I've always had a vision of spoiling my friends in this way. I covered the cost of the bnb, all they had to do was get there. In typical me fashion, I treated the trip like a PR trip for all of us -- inspired by the White Lotus press mailers I created an invite box that had a beach bag, custom sunnies (prada dupes), bucket hat, necklace, spritz supplies and the hand drawn invites. I used my cricut to add everyone's names in vinyl and created a ton of social media content about the creation of the whole thing. Those videos went semi-viral on TikTok and IG, racking up hundreds of thousands of views, and the brands showed up in the comments. I created a pitch deck to get them involved in the welcome bags and badda bing badda boom, it was a win win. They got content out of it, and my friends got goodies.
KD: What's the best part of working for yourself?
MW: The best part of working for yourself is also the worst part—you're your own boss. I joke with my friends all the time that my boss is a bitch and I'm a terrible employee. I love that I'm not beholden to anyone else and that I can truly make my life whatever I want it to be, but there is also a lot of pressure and isolation that comes with that.
As I've grown and built my team I've also had to learn that not everyone needs to know everything all the time. My greatest strength (having never worked corporate) can also be my greatest liability (not knowing status quo) especially when it comes to growing and scaling my team. There is SO MUCH in my business that happens behind the scenes, and things that I would NEVER post publicly on social media... but would gladly gab about over cocktails to trusted industry besties. At the end of the day, I wouldn't trade it for the world.
KD: On the flip side, what are some of the things (that Instagram may not see) about running your own company that you'd advise people they need to be ready for before going out on their own?
MW: There can be an uncomfortable amount of behind-the-scenes work and pressure that comes with running your own company. You have to be ready for the challenges of isolation, decision fatigue, and the responsibility of every choice impacting your business. There’s also a steep learning curve for the 'people skills' in entrepreneurship as you grow. But ultimately, health and mental health have been my biggest behind the scenes focus. I spent most of 2023 over-working, under-sleeping and chasing an income goal that wasn't sustainable if I wasn't making clear business decisions. This ultimately led to a bit of a menty b in Feb, which lead me down the path of therapy, neurofeedback, eliminating most caffeine, prioritizing sleep, and re-centering what I want my life to look like.
Entrepreneurship can be an addiction and, like all addictions—unhealthy. I had to keep telling myself that there was no point in working this hard just to work this hard if I can't also enjoy my life in a healthy way. I haven't taken time to share about this in detail on my social media but I hope I can now that I've come out the other side of it.
KD: Beyond work, what inspires you?
MW: FOOD! Food and experiences. I love the novelty of trying something totally new, in a new restaurant in a new country and the showmanship involved in the sharing of food as a cultural phenomenon. I love trying to brainstorm how a chef pulls a dish together, what techniques are used, and how everything comes together. Cooking is also one of the only things I do where I can really lose myself in the process and not look at a screen for hoooours. I love to host dinner parties for my friends in my one bedroom apartment and challenge myself to make something I've never made before. It gets all my creative juices flowing, and has become one of our favorite neighborhood traditions.
KD: What's next? What are you looking forward to as we approach 2025?
MW: In 2025, I'm looking forward to more opportunities to put in facetime with my team and our clients. Although we've worked virtually together for so long, I want to prioritize going to the client in person and really showing what we are capable of over a quick weekend when we are 100% tuned in to their brand. I would love to get to the point where brands are flying us out to overhaul their whole companies as an intensive or incubator. I'm also looking forward to more public speaking opportunities in San Diego and beyond!
I have *many* thoughts on this that I've been collecting and parsing through over the past couple days. As a consumer and a creator on this platform, I can only speak to my behavior. When I think of the newsletters I have a paid subscription to and find real ROI on, I think of:
- Jess Janz: my subscription allows me to attend her monthly poetry and writing workshops
- Carly Valancy: behind her paywall she shares real cold emails she has sent to grow her network, which is something I find valuable in my career right now
What's worth paying for will be different for everyone. Your essay on money was vulnerable and (I'm assuming) extremely cathartic for you. As a reader, though, I didn't feel there was a tangible takeaway that I could ascribe for myself. And I was hard pressed to find a takeaway from your Q&A with Katie in a newsletter that was all about the growing pains of making money and supporting oneself. She could have lent some really valuable recommendations or suggestions to your readers who are probably in the same boat.
And that's what I consider when thinking of where to spend my subscription dollars.
I think for writers (and the substack debate), it comes back to the reader. What tangible value are you providing to your reader -- especially if you're looking to create an additional income source with longevity.
I myself do not have a paywall (and do not have plans to implement one in the future). I will, however, begin charging for workshops that I've previously held for free and using my newsletter to promote them.
You mentioned that your top performing posts are your curated recommendations (particularly travel!). As a reader, I'd much rather pay for a living document with your recommendations since I know they're well-researched and trustworthy. The value for me would be huge -- it's a time saver! And people would pay for that.
Anyways! This was long-winded, but I wanted to share my thoughts since you asked for different perspectives.